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244988

Sigma-Aldrich

Bis(1,5-cyclooctadiene)nickel(0)

Sinônimo(s):

Bis(cyclooctadiene)nickel, Ni(COD)2

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About This Item

Fórmula empírica (Notação de Hill):
C16H24Ni
Número CAS:
1295-35-8
Peso molecular:
275.06
Número CE:
215-072-0
Número MDL:
MFCD00058902
Código UNSPSC:
12352202
ID de substância PubChem:
24854723
NACRES:
NA.22
Preço e disponibilidade não estão disponíveis no momento.

Nível de qualidade

200

adequação da reação

core: nickel
reaction type: Cross Couplings
reagent type: catalyst

Parâmetros

temperature sensitive

pf

60 °C (dec.) (lit.)

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

[Ni].C1CC=CCCC=C1.C2CC=CCCC=C2

InChI

1S/2C8H12.Ni/c2*1-2-4-6-8-7-5-3-1;/h2*1-2,7-8H,3-6H2;/b2*2-1-,8-7-;

chave InChI

JRTIUDXYIUKIIE-KZUMESAESA-N

Categorias relacionadas

Aplicação

Catalyst for the cycloaddition of 1,3-dienes.[1]
Reactant for:
  • Oxidative addition reactions

Catalyst for:
  • Asymmetric α-arylation and heteroarylation of ketones with chloroarenes
  • Cross-coupling reactions
  • Regioselective and stereoselective carboxylation/cyclization of allenyl aldehydes under a carbon dioxide atmosphere
  • Methyl carboxylation of homopropargylic alcohols
  • Stereoselective borylative ketone-diene coupling
  • Cycloaddition of benzamides with internal alkynes
Used to catalyze the addition of allyl phenyl sulfide to alkynes leading to 1,4-dienes. The reaction with terminal acetylenes proceeds in high yield and high selectivity. A variety of functional groups are tolerated.[2]

produto relacionado

Nº do produto
Descrição
Preços

06693

Timestrip Plus™ -20 °C

912794

Ni(COD)(DQ), ≥95%

Palavra indicadora

Danger

Frases de perigo

H228,H317,H351,H372

Classificações de perigo

Carc. 2 - Flam. Sol. 1 - Skin Sens. 1 - STOT RE 1

Órgãos-alvo

Lungs

Código de classe de armazenamento

4.1B - Flammable solid hazardous materials

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Escolha uma das versões mais recentes:

Certificados de análise (COA)

Lot/Batch Number
BCCJ4930
BCCH7614
BCCG3760
BCCH5546
BCCF6273

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Joachim Loup et al.
Angewandte Chemie (International ed. in English), 58(6), 1749-1753 (2018-12-06)
Highly enantioselective nickel-catalyzed alkene endo-hydroarylations were accomplished with full selectivity by organometallic C-H activation. The asymmetric assembly of chiral six-membered scaffolds proved viable in the absence of pyrophoric organoaluminum reagents within an unprecedented nickel/JoSPOphos manifold.
Qiang Gao et al.
Acta biomaterialia, 51, 112-124 (2017-01-31)
Numerous antimicrobial coatings have been developed for biomedical devices/implants, but few can simultaneously fulfill the requirements for antimicrobial and antifouling ability and biocompatibility. In this study, to develop an antimicrobial and antibiofilm surface coating, diblock amphiphilic molecules with antimicrobial and
Tsung-Han Lin et al.
ACS applied materials & interfaces, 9(5), 4948-4955 (2017-01-13)
The race for performance of integrated circuits is nowadays facing a downscale limitation. To overpass this nanoscale limit, modern transistors with complex geometries have flourished, allowing higher performance and energy efficiency. Accompanying this breakthrough, challenges toward high-performance devices have emerged
Journal of the American Chemical Society, 111, 6432-6432 (1989)
Addison N Desnoyer et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 25(20), 5259-5268 (2019-01-30)
The electronic nature of Ni π-complexes is underexplored even though these complexes have been widely postulated as intermediates in organometallic chemistry. Herein, the geometric and electronic structure of a series of nickel π-complexes, Ni(dtbpe)(X) (dtbpe=1,2-bis(di-tert-butyl)phosphinoethane; X=alkene or carbonyl containing π-ligands)
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Nickel complexes catalyze various synthetic reactions like oxidative addition, C-H activation, and cross-coupling.

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